Water → HCID 58016868, compound

HRID 1926915Notes

Reaction equation

HRID 1926915 reaction equation
O=[C:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:11]1([C@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:20][O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([NH:19][C@@H:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:18])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 988106-Oxoheptanoic acidHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 58016868HCID 58016868, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Put 8.80 g (55.63 mmol) 6-oxoheptanoic acid and 6.741 g (55.63 mmol) (R)-(+)-1-phenylethylamine together in 100 ml toluene at RT. Add a catalytic amount (approx. 50 mg) of p-toluenesulphonic acid and heat overnight with stirring on a water separator. Then partially concentrate by evaporation, filter off any solids using a paper filter, and fully concentrate the filtrate by evaporation. Dissolve the residue in 170 ml methanol. Add approx. 1.7 g Raney Nickel (moist with water) and hydrogenate for 48 h at 4 bar. Next, filter on diatomite and concentrate the filtrate by evaporation. Purify the residue by column chromatography on silica gel (solvent: dichloromethane/methanol 95:5), obtaining 4.15 g (48.5% of theor.) of the target compound, which is reacted without further characterization.

Workup

  1. customat RT
  2. temperatureheat overnight
  3. concentrationThen partially concentrate by evaporation
  4. filtrationfilter off any solids
  5. filtrationfilter
  6. concentrationfully concentrate the filtrate
  7. customby evaporation
  8. dissolutionDissolve the residue in 170 ml methanol
  9. additionAdd approx. 1.7 g Raney Nickel (moist with water)
  10. filtrationNext, filter on diatomite
  11. concentrationconcentrate the filtrate
  12. customby evaporation
  13. customPurify the residue by column chromatography on silica gel (solvent: dichloromethane/methanol 95:5)
  14. customobtaining 4.15 g (48.5% of theor.) of the target compound, which
  15. customis reacted without further characterization

Sources & evidence

ORD record
ord-0a4245012c6d4336a9ecedbb5dc334df
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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